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HRID742177

反应详情

EQUATION

反应方程式

HRID 742177 的结构方程式

REACTANTS

反应物

3
结构：CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O
HCID12560

Erythromycin

C37H67NO13

结构：[Na+].[OH-]
HCID14798

Sodium Hydroxide

HNaO

结构：F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2
HCID2724933

Selectfluor

C7H14B2ClF9N2

PRODUCTS

生成物

1
结构：CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@](C)(F)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O
HCID71260

Flurithromycin

C37H66FNO13

收率 87.8%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CC(=O)O
溶剂HCID176

Acetic Acid

C2H4O2

PROCEDURE

实验过程

Erythromycin A (5 g, 6.813 mmole) was dissolved in glacial acetic acid (20 mL) at room temperature and stirred for 2 hours. The pH of the mixture was adjusted to 4.3 with 6N sodium hydroxide (approx. 12.5 mL) while the temperature was maintained below 20° C. 1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (2.4 g, 6.813 mmole) was added and stirring continued for an additional 3 hours at 22° C. The reaction was worked up in the same manner as Example 1 to afford 4.5 g of crude flurithromycin. This material was recrystallized as described in Example 1 to yield 2.6 g (51% yield) of flurithromycin.

WORKUP

后处理

  1. temperaturewas maintained below 20° C
  2. stirringstirring
  3. waitcontinued for an additional 3 hours at 22° C